PL212887B1 - Podstawione pochodne cykloheksano-1,4-diaminy - Google Patents

Podstawione pochodne cykloheksano-1,4-diaminy

Info

Publication number: PL212887B1
Authority: PL; Poland
Prior art keywords: group; diamine; dimethyl; dihydrochloride; phenylcyclohexane
Prior art date: 2001-05-09

Application number

PL368851A

Other languages

English (en)

Polish (pl)

Other versions

PL368851A1 (en

Inventor

Bernd Sundermann

Hagen-Heinrich Hennies

Werner Englberger

Babette-Yvonne Kögel

Original Assignee

Gruenenthal Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-05-09

Filing date

2002-05-08

Publication date

2012-12-31

2002-05-08 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

2005-04-04 Publication of PL368851A1 publication Critical patent/PL368851A1/xx

2012-12-31 Publication of PL212887B1 publication Critical patent/PL212887B1/pl

Links

VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 title claims abstract 56
239000003814 drug Substances 0.000 claims abstract 17
208000002193 Pain Diseases 0.000 claims abstract 15
230000036407 pain Effects 0.000 claims abstract 7
238000004519 manufacturing process Methods 0.000 claims abstract 5
-1 adamantanyl Chemical group 0.000 claims 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 55
229910052739 hydrogen Inorganic materials 0.000 claims 54
239000001257 hydrogen Substances 0.000 claims 54
229920006395 saturated elastomer Polymers 0.000 claims 54
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 51
150000002431 hydrogen Chemical class 0.000 claims 45
239000000203 mixture Substances 0.000 claims 35
150000003839 salts Chemical class 0.000 claims 30
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 28
125000001041 indolyl group Chemical group 0.000 claims 28
125000006239 protecting group Chemical group 0.000 claims 27
150000001875 compounds Chemical class 0.000 claims 25
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 20
239000002253 acid Substances 0.000 claims 20
150000007513 acids Chemical class 0.000 claims 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 17
125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims 15
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 15
125000001624 naphthyl group Chemical group 0.000 claims 15
125000001544 thienyl group Chemical group 0.000 claims 15
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 14
125000000217 alkyl group Chemical group 0.000 claims 14
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 13
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 13
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 13
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 13
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 13
150000001768 cations Chemical class 0.000 claims 10
238000000034 method Methods 0.000 claims 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
239000004480 active ingredient Substances 0.000 claims 9
125000000753 cycloalkyl group Chemical group 0.000 claims 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
208000000094 Chronic Pain Diseases 0.000 claims 4
230000001154 acute effect Effects 0.000 claims 4
208000005298 acute pain Diseases 0.000 claims 4
239000003153 chemical reaction reagent Substances 0.000 claims 4
208000004296 neuralgia Diseases 0.000 claims 4
230000002981 neuropathic effect Effects 0.000 claims 4
208000021722 neuropathic pain Diseases 0.000 claims 4
238000006268 reductive amination reaction Methods 0.000 claims 4
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 3
239000013543 active substance Substances 0.000 claims 3
150000004795 grignard reagents Chemical class 0.000 claims 3
OTCYOBLTAQTFPW-UHFFFAOYSA-N 4-aminocyclohexan-1-one Chemical class NC1CCC(=O)CC1 OTCYOBLTAQTFPW-UHFFFAOYSA-N 0.000 claims 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 1
FTCXWNUJMSGUKP-UHFFFAOYSA-N 1-amino-4-oxocyclohexane-1-carbonitrile Chemical compound N#CC1(N)CCC(=O)CC1 FTCXWNUJMSGUKP-UHFFFAOYSA-N 0.000 claims 1
DSAMTIPDNZRRDB-UHFFFAOYSA-N 1-n,1-n-dimethyl-1-phenyl-4-n-propylcyclohexane-1,4-diamine;hydrochloride Chemical compound Cl.C1CC(NCCC)CCC1(N(C)C)C1=CC=CC=C1 DSAMTIPDNZRRDB-UHFFFAOYSA-N 0.000 claims 1
YWKWGULBAVUUNJ-UHFFFAOYSA-N 4-n-(1h-indol-3-ylmethyl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1CC(NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 YWKWGULBAVUUNJ-UHFFFAOYSA-N 0.000 claims 1
UVDJEWBPNJXYBU-UHFFFAOYSA-N 4-n-(2,3-dihydro-1h-inden-2-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical class Cl.Cl.C1CC(NC2CC3=CC=CC=C3C2)CCC1(N(C)C)C1=CC=CC=C1 UVDJEWBPNJXYBU-UHFFFAOYSA-N 0.000 claims 1
FNYVYGDTRKLTQD-UHFFFAOYSA-N 4-n-(9-ethylcarbazol-3-yl)-1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(CC1)CCC1(N(C)C)C1=CC=CC=C1 FNYVYGDTRKLTQD-UHFFFAOYSA-N 0.000 claims 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
239000005695 Ammonium acetate Substances 0.000 claims 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
239000007818 Grignard reagent Substances 0.000 claims 1
101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
125000005219 aminonitrile group Chemical group 0.000 claims 1
229940043376 ammonium acetate Drugs 0.000 claims 1
235000019257 ammonium acetate Nutrition 0.000 claims 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical class N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
125000002524 organometallic group Chemical group 0.000 claims 1
150000002923 oximes Chemical class 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
230000002829 reductive effect Effects 0.000 claims 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims 1
230000002093 peripheral effect Effects 0.000 abstract 2
208000036487 Arthropathies Diseases 0.000 abstract 1
206010012735 Diarrhoea Diseases 0.000 abstract 1
206010061218 Inflammation Diseases 0.000 abstract 1
208000012659 Joint disease Diseases 0.000 abstract 1
229940035676 analgesics Drugs 0.000 abstract 1
239000000730 antalgic agent Substances 0.000 abstract 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000002955 immunomodulating agent Substances 0.000 abstract 1
230000002757 inflammatory effect Effects 0.000 abstract 1
230000004054 inflammatory process Effects 0.000 abstract 1
208000002551 irritable bowel syndrome Diseases 0.000 abstract 1
210000004872 soft tissue Anatomy 0.000 abstract 1

Classifications

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- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
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Addiction (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
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Diabetes (AREA)
Urology & Nephrology (AREA)
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Rheumatology (AREA)
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PL368851A 2001-05-09 2002-05-08 Podstawione pochodne cykloheksano-1,4-diaminy PL212887B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10123163A DE10123163A1 (de)	2001-05-09	2001-05-09	Substituierte Cyclohexan-1,4-diaminderivate

Publications (2)

Publication Number	Publication Date
PL368851A1 PL368851A1 (en)	2005-04-04
PL212887B1 true PL212887B1 (pl)	2012-12-31

Family

ID=7684562

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
PL368851A PL212887B1 (pl)	2001-05-09	2002-05-08	Podstawione pochodne cykloheksano-1,4-diaminy
PL366662A PL220595B1 (pl)	2001-05-09	2002-05-08	Podstawione pochodne 2-pirydyno-cykloheksano-1,4-diaminy, sposób ich wytwarzania, zastosowanie oraz środek leczniczy zawierający te pochodne
PL02366631A PL366631A1 (en)	2001-05-09	2002-05-09	Substituted cyclohexan-1,4-diamine derivatives with constipating and peripheral analgesic properties

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
PL366662A PL220595B1 (pl)	2001-05-09	2002-05-08	Podstawione pochodne 2-pirydyno-cykloheksano-1,4-diaminy, sposób ich wytwarzania, zastosowanie oraz środek leczniczy zawierający te pochodne
PL02366631A PL366631A1 (en)	2001-05-09	2002-05-09	Substituted cyclohexan-1,4-diamine derivatives with constipating and peripheral analgesic properties

Country Status (30)

Country	Link
US (3)	US6998409B2 (cs)
EP (3)	EP1392641B1 (cs)
JP (3)	JP2004533439A (cs)
KR (2)	KR20040002943A (cs)
CN (2)	CN1533374B (cs)
AR (1)	AR035883A1 (cs)
AT (2)	ATE359260T1 (cs)
AU (3)	AU2002341195B2 (cs)
BR (2)	BR0209580A (cs)
CA (3)	CA2446461C (cs)
CO (2)	CO5540300A2 (cs)
CY (2)	CY1106468T1 (cs)
CZ (2)	CZ20032995A3 (cs)
DE (3)	DE10123163A1 (cs)
DK (2)	DK1385825T3 (cs)
EC (2)	ECSP034830A (cs)
ES (2)	ES2291486T3 (cs)
HU (3)	HU229288B1 (cs)
IL (4)	IL158784A0 (cs)
MX (3)	MXPA03010201A (cs)
NO (2)	NO326784B1 (cs)
NZ (2)	NZ529334A (cs)
PE (1)	PE20021094A1 (cs)
PL (3)	PL212887B1 (cs)
PT (2)	PT1385825E (cs)
RU (2)	RU2287523C2 (cs)
SI (2)	SI1385825T1 (cs)
SK (2)	SK286617B6 (cs)
WO (3)	WO2002090330A1 (cs)
ZA (2)	ZA200309522B (cs)

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2001
- 2001-05-09 DE DE10123163A patent/DE10123163A1/de not_active Withdrawn
2002
- 2002-05-08 AT AT02738038T patent/ATE359260T1/de active
- 2002-05-08 PT PT02750900T patent/PT1385825E/pt unknown
- 2002-05-08 NZ NZ529334A patent/NZ529334A/en not_active IP Right Cessation
- 2002-05-08 AT AT02750900T patent/ATE370120T1/de active
- 2002-05-08 IL IL15878402A patent/IL158784A0/xx unknown
- 2002-05-08 KR KR10-2003-7014530A patent/KR20040002943A/ko not_active Ceased
- 2002-05-08 BR BR0209580-7A patent/BR0209580A/pt not_active Application Discontinuation
- 2002-05-08 MX MXPA03010201A patent/MXPA03010201A/es active IP Right Grant
- 2002-05-08 BR BR0209579-3A patent/BR0209579A/pt active Search and Examination
- 2002-05-08 IL IL15878202A patent/IL158782A0/xx unknown
- 2002-05-08 WO PCT/EP2002/005078 patent/WO2002090330A1/de not_active Ceased
- 2002-05-08 CZ CZ20032995A patent/CZ20032995A3/cs unknown
- 2002-05-08 NZ NZ529147A patent/NZ529147A/en not_active IP Right Cessation
- 2002-05-08 DE DE50210707T patent/DE50210707D1/de not_active Expired - Lifetime
- 2002-05-08 KR KR1020037014568A patent/KR100895778B1/ko not_active Expired - Fee Related
- 2002-05-08 DE DE50209929T patent/DE50209929D1/de not_active Expired - Lifetime
- 2002-05-08 PL PL368851A patent/PL212887B1/pl unknown
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- 2002-05-08 HU HU0400989A patent/HU229288B1/hu not_active IP Right Cessation
- 2002-05-08 WO PCT/EP2002/005051 patent/WO2002090317A1/de not_active Ceased
- 2002-05-08 ES ES02750900T patent/ES2291486T3/es not_active Expired - Lifetime
- 2002-05-08 PL PL366662A patent/PL220595B1/pl unknown
- 2002-05-08 SK SK1378-2003A patent/SK286617B6/sk not_active IP Right Cessation
- 2002-05-08 DK DK02750900T patent/DK1385825T3/da active
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- 2002-05-08 JP JP2002587410A patent/JP2004528374A/ja active Pending
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2003
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2007
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Also Published As

Publication number	Publication date
CO5700725A2 (es)	2006-11-30
SI1392641T1 (sl)	2007-10-31
KR100895778B1 (ko)	2009-05-08
NO326784B1 (no)	2009-02-16
US20040147741A1 (en)	2004-07-29
AU2002312883B2 (en)	2007-09-06
BR0209580A (pt)	2004-06-22
CY1106468T1 (el)	2012-01-25
CN1533374A (zh)	2004-09-29
EP1392641A1 (de)	2004-03-03
DK1392641T3 (da)	2007-07-16
DE50209929D1 (de)	2007-05-24
HUP0400888A2 (hu)	2004-07-28
ECSP034830A (es)	2004-03-23
CA2446463C (en)	2010-07-13
CA2446463A1 (en)	2002-11-14
CZ20032995A3 (cs)	2004-02-18
EP1392641B1 (de)	2007-04-11
HUP0400989A3 (en)	2011-08-29
SK13792003A3 (sk)	2004-06-08
KR20040017214A (ko)	2004-02-26
EP1385493A1 (de)	2004-02-04
CO5540300A2 (es)	2005-07-29
JP2005515959A (ja)	2005-06-02
MXPA03010195A (es)	2004-03-10
AU2007202033B2 (en)	2010-02-04
SK287319B6 (sk)	2010-07-07
ES2284876T3 (es)	2007-11-16
DE50210707D1 (de)	2007-09-27
RU2003134145A (ru)	2005-05-20
DK1385825T3 (da)	2007-11-05
NO20034930L (no)	2004-01-05
ATE370120T1 (de)	2007-09-15
NZ529334A (en)	2004-10-29
SK13782003A3 (sk)	2004-04-06
NZ529147A (en)	2006-10-27
WO2002090330A1 (de)	2002-11-14
ECSP034831A (es)	2004-03-23
CA2446461A1 (en)	2002-11-14
CA2446735A1 (en)	2002-11-14
US20040162287A1 (en)	2004-08-19
EP1385825A1 (de)	2004-02-04
AR035883A1 (es)	2004-07-21
WO2002089783A1 (de)	2002-11-14
NO20034930D0 (no)	2003-11-05
PT1385825E (pt)	2007-09-04
CN1307158C (zh)	2007-03-28
US6998409B2 (en)	2006-02-14
BR0209579A (pt)	2004-06-22
HUP0400888A3 (en)	2008-03-28
HUP0400963A2 (hu)	2004-08-30
MXPA03010201A (es)	2006-02-09
CZ20033005A3 (en)	2004-03-17
JP2004528374A (ja)	2004-09-16
PT1392641E (pt)	2007-05-31
RU2003134147A (ru)	2005-05-20
PL366631A1 (en)	2005-02-07
MXPA03010134A (es)	2004-03-10
PL220595B1 (pl)	2015-11-30
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PL212887B1 (pl)	2012-12-31	Podstawione pochodne cykloheksano-1,4-diaminy
DE10252650A1 (de)	2004-05-27	Cyclohexyl-Harnstoff-Derivate
JP4208139B2 (ja)	2009-01-14	置換された４−アミノシクロヘキサノール
PL217415B1 (pl)	2014-07-31	Podstawione 4-aminocykloheksanole, środek leczniczy zawierający podstawiony 4-aminocykloheksanol, zastosowanie podstawionego 4-aminocykloheksanolu oraz sposoby wytwarzania podstawionych 4-aminocykloheksanoli
US7678834B2 (en)	2010-03-16	Substituted 4-aminocyclohexanol compounds